Polyglycol ether surface-active agents



Un t d States. QtenrO No Drawing. Application January 24, 1957 I 'Serial No. 635,964 I 16 Clalms. (Cl. 260-613) --This invention relates to new monoethers of polyoxyalkylene glycols.

I Step 1.-Reaction of tridecyl alcohol with styrene oxide Ten grams of solid KOH were dissolved in 825 g..

... to produce 478 g. of tridecyl monoether of styrene glycol, boiling point 185-195 C./3 mm.; N 1.5010; d

' The compounds of the. invention correspond to the 7 wherein R is an unsubstituted alkyl-radical containing to 18 carbon atoms or a phenyl, alkylph enyl or chlorinated phenyl radica1, X is a phenylethylene radical,

(alkylene-OL, is. a 'polyoxyalkylene' chain wherein the. alkylene'radicals are vicinal alkyl'ene radicals and each' contains 2 to 4 carbon atoms and n is a number in the range of-about 5 to 50. By vicinal alkylene radicals we means those having points of attachment on adjacent carbon atoms. Such radicals include CH CH "C 'H CH(CH --CH CH(C H and but not CH CH CH or --CH CH CH(CH The above-defined compounds are synthetic lubricants or surface-active materials having exceptional utility as wetting agents, emulsifiers, detergents or antifoam agents, depending on the particular compound'used. .j-

While the compounds corresponding to the 'abovefore mula may be made by any suitable process, a preferred process comprises reacting styrene oxide and a monohydric alcohol or phenol, ROH, whereby a styrene glycol monoether is formed, and then reacting said monoether with the appropriate alkylene oxide or oxides. Alternatively, styrene glycol can be consecutively etherified with the alcohol, ROH, and with the polyoxyalkylene glycol, HO(alkylene-O),,H. Other methods for making the 2,888,489 I I Patented May 2 6, 1959 compounds will be apparent to those. skilled in the art. .The following'examples illustrate the. practice of the invention.

EXAMPLE 1 (4.125 m.) of oxo-process tridecyl alcohol. I The solution was then maintained at ISO-160 C. while 600 g."(5 m;) of styrene oxide were added. The product was distilled 0.9580; and OH analysis, 4.98 percent (theor., 5.30). Step 2.--Az idition of alkylene oxide Two grams of KOI Iwere dissolved inl l6 (0.362ni.) of the product of Step 1 and the resulting solution was maintained at 100-125" C. While 190 g. (4.34- m.) of ethylene oxidewere reacted with it. The product was neutralized with carbon dioxide and filtered. It was a soft tan wax, highly soluble in water and possessing valuable surfactant properties.

, Instead of the tridecyl alcohol used in the above example we may useother alkanols containing 2 to 18,- carbon atoms, phenol, alkylphenols or chlorophenols Instead of the ethylene oxide we may use 1,2-propylene. oxide, 1,2 or 2,3-butylene oxide or mixtures of any of; these oxides- When more than one oxide is to b e used. in a compound they may be reacted separately,-in sequence, or theymay be mixed and reacted simultaneously; Instead of the KOH used as catalyst, we may useuany alkaline catalyst such. as thealkaliland alkaline earth metal alkoxides, oxides, or hydroxides or tert. alky1 amines. The reaction temperature is preferably in the range of about 100-180 C. and the pressure is prefer;

. ably aboutO- to 50 pounds per square inch, guage.

Tables I and 11 show some typical productsillustrative.

of the invention, together with some of their physical and chemical properties. The data in Table II show the. wide range of surfactant properties obtainable by suitable choice of the hydroxyl reactant, ROH, and by. varying. the size and number of oxyalkylene groups in the po1yoxyalkylene chain. Thus, the compounds ofExamplevl-Bq;

are excellent detergents and wetting and emulsifying agents while those of Examples 4 and 5 are substantially insoluble in water but are powerful anti-foam agents. Similarly, the products of Examples 6-8 and 12 are good wetting agents while those of Examples 9-11 are poor wetting agents but are good emulsifiers. That of Example 9 is an especially valuable emulsifier for use in surfacecoating products, such as latex paints.

TABLE I.G OMPOUNDS RO-X-O-(ALKYLENE-O) n-H Moles Alkylene Oxides Percent Ex. N o. R 011 Na" d}:

BO P0 E0 1 Trldeey 12 2. 54 2 rln 16 1.77

3 16 2. 09 4 8 3. 70 1. 4710 0. 9950 6 6 4. 55 1. 4750 0. 9713 6 5 10 3. 08 1. 4728 1. 0280 7 5 5 3. 28 1. 4750 1. 0255 5 5 8. 15' 1. 4740 1. 0218 10 3. 00 10 2. 1. 5070 1. 1270 11 rin 30 2. 32 Solid Solid 12 Di Sec. Butylphenyl 10 2. 51 1. 5060 1. 0710 i; n 5 10 2. 62 1. 4902 1. 0510 14 2,4-Dichloropheny 10 3. 49 1. 5177 1 1827 Moles oi 1,2-butylene oxide (B 0), 1,2-propylene oxide (P0) and/or ethylene oxide (E0) used in forming the polyoxyalkylene chain. Where two alkylene oxides were used, the addition was consecutive, with the ethylene oxide being added last, except for Example 8, where the two oxides were added simultaneously. 

1. A COMPOUND CORRESPONDING TO THE FORMULA
 6. A COMPOUND AS DEFINED IN CLAIM 1 WHEREIN R IS A PHENYL RADICAL. 